A surprising new route to 4-nitro-3-phenylisoxazole

A surprising new route to 4-nitro-3-phenylisoxazole

A one-pot synthesis of 4-nitro-3-phenylisoxazole has been carried out by treatment of cinnamyl alcohol dissolved in acetic acid with sodium nitrite; in addition, 4-phenyl-3-furoxanmethanol was obtained in 40% yield.

Bibliographic Details
Main Authors:	Henning Hopf, Aboul-fetouh E. Mourad, Peter G. Jones
Format:	Article
Language:	English
Published:	Beilstein-Institut 2010-06-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	cinnamyl alcohol furoxan derivatives isoxazole derivatives X-ray diffraction
Online Access:	https://doi.org/10.3762/bjoc.6.68

Similar Items

Crystal structure and Hirshfeld surface analysis of ethyl 5-phenylisoxazole-3-carboxylate
by: Althaf Shaik, et al.
Published: (2017-04-01)

Synthesis and Antitumor Evaluation of Novel Hybrids of Phenylsulfonylfuroxan and Estradiol Derivatives
by: Qi Wan, et al.
Published: (2020-02-01)

Flavouring Group Evaluation 214: alpha, beta‐Unsaturated aldehydes and precursors from chemical subgroup 3.1 of FGE.19: Cinnamyl derivatives
by: European Food Safety Authority (EFSA)
Published: (2009-04-01)

Flavouring Group Evaluation 216: alpha, beta‐Unsaturated aldehydes from chemical subgroup 3.3 of FGE.19: 2‐Phenyl‐2‐alkenals
by: European Food Safety Authority (EFSA)
Published: (2009-04-01)

5-[(Benzo[d][1,3]dioxol-5-yl)methyl]-3-[4-(pyridin-2-yl)phenyl]-4,5-dihydroisoxazole
by: Nasseem El-Khatatneh, et al.
Published: (2017-02-01)

Synthesis, structure and toxicity evaluation of ethanolamine nitro/chloronitrobenzoates: a combined experimental and theoretical study
by: Manuela Crisan, et al.
Published: (2017-12-01)

Supramolecular structures based on regioisomers of cinnamyl-α-cyclodextrins – new media for capillary separation techniques
by: Gabor Benkovics, et al.
Published: (2016-01-01)

Crystal structure of 5-{3-[2,6-dimethyl-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]propyl}-N-(11-hydroxyundecyl)isoxazole-3-carboxamide hemihydrate
by: K. Salorinne, et al.
Published: (2015-05-01)

Microwave-Assisted Kabachnik–Fields Reaction with Amino Alcohols as the Amine Component
by: Ádám Tajti, et al.
Published: (2019-04-01)

Functionalized multi walled carbon nanotubes supported copper-titania nanoparticles for oxidation of cinnamyl alcohol under mild reaction conditions
by: Zahoor Iqbal, et al.
Published: (2021-01-01)

Unusual reaction of 3,4-bis(3-nitrofurazan-4-yl)furoxan with ammonia, primary amines and hydrazine
by: Astrat’ev Alexander, et al.
Published: (2012-08-01)

Synthesis and Antimicrobial Activity of N′-Heteroarylidene-1-adamantylcarbohydrazides and (±)-2-(1-Adamantyl)-4-acetyl-5-[5-(4-substituted phenyl-3-isoxazolyl)]-1,3,4-oxadiazolines
by: Abdul-Malek S. Al-Tamimi, et al.
Published: (2012-03-01)

Synthesis and anti-nociceptive potential of isoxazole carboxamide derivatives
by: Hajira Bibi, et al.
Published: (2019-01-01)

Structural study and Hirshfeld surface analysis of (Z)-4-(2-methoxybenzylidene)-3-phenylisoxazol-5(4H)-one
by: Assia Benouatas, et al.
Published: (2021-05-01)

Synthesis, Crystal Structure, and Biological Evaluation of a Series of Phloretin Derivatives
by: Li Wang, et al.
Published: (2014-10-01)

Biochemical Characterization of the Rice Cinnamyl Alcohol Dehydrogenase Gene Family
by: Hye Lin Park, et al.
Published: (2018-10-01)

Crystal structure of (R)-5-[(R)-3-(4-chlorophenyl)-5-methyl-4,5-dihydroisoxazol-5-yl]-2-methylcyclohex-2-enone
by: Ali Oubella, et al.
Published: (2020-03-01)

Characterization of the Materials Synthesized by High Pressure-High Temperature Treatment of a Polymer Derived t-BC2N Ceramic
by: Gabriela Mera, et al.
Published: (2011-11-01)

Assessment of potential winter hardiness in winter bread wheat cultivars and genotypes by analyzing autofluorescence in seedling tissues
by: I. V. Karkhardin, et al.
Published: (2021-04-01)

A cinnamyl alcohol dehydrogenase required for sclerotial development in Sclerotinia sclerotiorum
by: Jiahong Zhou, et al.
Published: (2020-06-01)

Deep Eutectic Solvents as Smart Cosubstrate in Alcohol Dehydrogenase-Catalyzed Reductions
by: Santiago Nahuel Chanquia, et al.
Published: (2020-09-01)

Nitro-, Cyano-, and Methylfuroxans, and Their Bis-Derivatives: From Green Primary to Melt-Cast Explosives
by: Alexander A. Larin, et al.
Published: (2020-12-01)

Perylenequione Derivatives with Anticancer Activities Isolated from the Marine Sponge-Derived Fungus, Alternaria sp. SCSIO41014
by: Xiaoyan Pang, et al.
Published: (2018-08-01)

Understanding Chemistry and Unique NMR Characters of Novel Amide and Ester Leflunomide Analogues
by: Morkos A. Henen, et al.
Published: (2017-12-01)

An Isoxazole Derivative SHU00238 Suppresses Colorectal Cancer Growth through miRNAs Regulation
by: Haoyu Wang, et al.
Published: (2019-06-01)

Three New Sesquiterpenoids and One New Sesquiterpenoid Derivative from Chinese Eaglewood
by: Huan Zhao, et al.
Published: (2016-02-01)

Synthesis, Crystal Structure and Anti-Fatigue Effects of Some Benzamide Derivatives
by: Xianglong Wu, et al.
Published: (2014-01-01)

Furoxan derivatives demonstrated in vivo efficacy by reducing Mycobacterium tuberculosis to undetectable levels in a mouse model of infection
by: P.C. de Souza, et al.
Published: (2020-10-01)

Nucleophilic dearomatization of 4-aza-6-nitrobenzofuroxan by CH acids in the synthesis of pharmacology-oriented compounds
by: Alexey M. Starosotnikov, et al.
Published: (2017-12-01)

<i>CAD</i> Genes: Genome-Wide Identification, Evolution, and Their Contribution to Lignin Biosynthesis in Pear (<i>Pyrus bretschneideri</i>)
by: Kaijie Qi, et al.
Published: (2021-07-01)

Efficient biosynthesis of cinnamyl alcohol by engineered Escherichia coli overexpressing carboxylic acid reductase in a biphasic system
by: Chen Zhang, et al.
Published: (2020-08-01)

Heck Transformations of Biological Compounds Catalyzed by Phosphine-Free Palladium
by: Stanisława Tarnowicz-Ligus, et al.
Published: (2018-09-01)

The cinnamyl alcohol dehydrogenase (CAD) gene family in flax (Linum usitatissimum L.): Insight from expression profiling of cads induced by elicitors in cultured flax cells
by: Eom Hee Seung, et al.
Published: (2016-01-01)

Nitroimidazoles XIII. Synthesis of Substituted (1-Methyl-5-Nitro-2-Imidazolyl) Isoxazoles
by: Abbas Shafiee, et al.
Published: (1998-12-01)

Synthesis and Crystal Structure of A Pyrithione Derivative: Bis{2-[(1-oxidopyridin-2-yl)sulfanyl]-4,5-dihydro-1<i>H</i>-imidazol-3-ium} tetrachlorocuprate(2-)
by: Łukasz Balewski, et al.
Published: (2019-06-01)

Atrans-Dinitrodiazenofuroxan Isomers-A DFT Treatise Lemi Türker
by: Lemi Türker
Published: (2019-08-01)

Atrans-Dinitrodiazenofuroxan Isomers-A DFT Treatise Lemi Türker
by: Lemi Türker
Published: (2019-08-01)

Selective Oxidation of Cinnamyl Alcohol to Cinnamaldehyde over Functionalized Multi-Walled Carbon Nanotubes Supported Silver-Cobalt Nanoparticles
by: Zahoor Iqbal, et al.
Published: (2021-07-01)

Characterization of Two New brown midrib1 Mutations From an EMS-Mutagenic Maize Population for Lignocellulosic Biomass Utilization
by: Wangdan Xiong, et al.
Published: (2020-11-01)

Overexpression of Artemisia annua Cinnamyl Alcohol Dehydrogenase Increases Lignin and Coumarin and Reduces Artemisinin and Other Sesquiterpenes
by: Dongming Ma, et al.
Published: (2018-06-01)